Patients on anticoagulation therapy, particularly those on warfarin, are at risk of gastrointestinal bleeding, gum bleeding, hematuria, and ecchymosis. However, it is rare for such patients to present with intramural or submucosal bleeding leading to intestinal obstructive symptoms. Sub-mucosal intestinal bleeding due to prolonged anticoagulant use is uncommon. Literature suggests that the duodenum and small intestine are common locations for anticoagulant-induced hematomas, occurring in approximately 1 case per 2,500 anticoagulated patients per year. However, intramural colonic hematomas are rarely reported. Spontaneous anticoagulant induced hematomas may develop as early as 10 days after starting therapy. We report the case of a 63-year-old female who presented with recto-sigmoid sub-mucosal bleeding causing obstructive symptoms. The patient was managed surgically with laparotomy, resulting in significant improvement, and was scheduled for follow-up to evaluate the feasibility of reintroducing anticoagulation therapy.